Water → HCID 13228382, compound

HRID 647623Notes

Reaction equation

HRID 647623 reaction equation
[CH:1]([N-]C(C)C)([CH3:3])[CH3:2].[Li+].[Cl:9][C:10]1[CH:31]=[CH:30][C:13]2[C:14]3[C:15](=[CH:26][NH:27][C:28]=3[CH3:29])[CH2:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:12]=2[CH:11]=1.C(Br)C#C.O>O1CCCC1.C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:31]=[CH:30][C:13]2[C:14]3[C:15](=[C:26]([CH2:3][C:1]#[CH:2])[NH:27][C:28]=3[CH3:29])[CH2:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:12]=2[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 2724682Lithium diisopropylamideHCID 13067095HCID 13067095, compound

Product 1

HCID 13228382HCID 13228382, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

By means of a syringe 7 ml (4.2 mmole) of a 0.62 M tetrahydrofuran solution of lithium diisopropylamide was added dropwise to a solution of 1.3 g (4.0 mmole) of 8-chloro-6-(2-fluorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine in 30 ml of dry tetrahydrofuran which was cooled to -20° C. The solution was stirred at -20° C. for 5 minutes followed by the addition of 2.4 ml (25 mmole) of 80% propargyl bromide in toluene. The mixture was allowed to warm to room temperature and stirred for 2 hours. Water was added and the mixture was extracted with ether. The ether solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to give an amber foam. Purification by column chromatography (silica gel, 20 g; eluent 5% ether in methylene chloride) gave a foam. Crystallization from a mixture of ether and petroleum ether gave cream prisms. (mp 179-180).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hours
  3. extractionthe mixture was extracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto give an amber foam
  8. customPurification by column chromatography (silica gel, 20 g; eluent 5% ether in methylene chloride)
  9. customgave a foam
  10. customCrystallization
  11. additionfrom a mixture of ether and petroleum ether
  12. customgave cream prisms

Sources & evidence

ORD record
ord-9fc8fbf59ec74f3a9b718d6b6a794aa1
Source dataset
uspto-grants-1983_10
Patent number
US04409390

Reaction notes

Loading…